Work Text:
Elizabeth picked up the last paper in her inbox and reviewed it. Another travel expense for her to process, this one for dinner at a clearly upscale restaurant. Was this even business-related, or was it a date night Robert disguised as a business expense? She wondered this a lot, but always predicted the latter, given that her boss was a successful entrepreneur in the men’s fashion space, most known for his line of suits and modern casual clothes that were affordable yet designed to look trendy to allow buyers to feel more confident. Of course he was one of the most eligible bachelors in Chicago.
She never had any plans to work at RR Apparel or in the fashion industry. Her last assistant job had been with a Chicago lawyer, but she didn’t like how her old boss took advantage of her and often asked her to run lunch or coffee errands. Robert occasionally asked for that, of course, but also trusted Elizabeth with reimbursements, booking travel, and overseeing his calendar. Plus, she admired that he built a successful brand in Chicago, which seemed unlikely when he first started given that New York was the heart and soul of the fashion industry.
Elizabeth loved being a personal assistant because she was organized and got a lot of satisfaction out of crossing off a to-do list and keeping others happy. She was hoping that one day, she could move out to New York or LA to seek more opportunities working with celebrities or high-profile executives similar to Robert.
“Elizabeth, good morning!” Robert exclaimed as he strolled into the office. “You’re looking nice today.” He nodded to her necklace with white and blue pearls and a blue sleeveless top with black pants. Although she worked at a fashion company, she still preferred a more classic style.
“Thanks.” She kept her voice neutral, as she felt weird when he complimented her on her outfit or hair, although she was simultaneously flattered. Besides, the good parts of the job outweighed this one negative part, and he never crossed any lines or harassed her.
“Get those reimbursements done yet?” he asked.
“Not quite. I just put the last one in. I’m not sure if you recall, but I prefer to enter all of the expenses and then get the reimbursements over to Shirley.”
“As long as I get my money back, then I don’t judge your systems. But now that you’re done with that, I need you to help Kerry start getting the word out about the fifth anniversary of the line. See what she needs from you; I imagine it will be social media posts or sending announcements to the press. Call that guy from the Tribune back and reschedule my interview; I just had another meeting come up that day with ABC. They want me to be on Shark Tank. Oh, and you know I hate to ask you this, but can you order lunch for the all-staff meeting on Friday? We need to start planning for the anniversary now.”
“Sure…wait…” She pulled up her calendar and frowned. “This is the first I’m hearing of this all-staff meeting. And Janet’s still out…shouldn’t we have this when she gets back?”
“Thought I mentioned it to you. Well, tell everyone it’s happening and get lunch. Send Janet an email and see if she’d mind calling in after that leadership summit thing she’s at. Something or other for women in business. I’m sure they should be done by Friday at noon. Thanks Elizabeth!” He headed into his office and closed the door behind him.
Before Elizabeth could even pick up her phone to call the Tribune, Shirley appeared at her desk. Shirley worked in the accounting department, having originally been a bookkeeper before she went back to school. Now she’d been out for a year and was working under John, the finance director, to master her first accountant role.
“Hey,” Shirley said, trying to keep her voice down. “I thought I saw Robert come in. Did you avoid any inappropriate compliments?”
“He told me I look nice, but nothing beyond that. I mean, there’s worse things he could say, right?”
“Well, you’re great at your job, and you should be valued for more than being attractive. But I admit, you did get a pretty nice Christmas gift from him. I know as the CEO’s personal assistant you get some good perks. It was champagne, right? I mean, all I got was a tumbler with the company logo and a gift card. You’d think that John would have done a little bit more given that he’s the finance director and inherited family wealth. Maybe next year, though, right?”
“Cross your fingers.
“I know this sounds random,” Elizabeth continued. “But I do have a bit of a dilemma. I think Robert and I are starting to crush on each other. Nothing happened at the Christmas party or anything, but it’s the way he looks at me and respects me and gives me all this extra responsibility…”
“You’re one of the best assistants he’s ever had; he’s told me that himself.” Shirley started laughing. “Of course he’s going to compliment you…but how could you even have a crush on someone like him?"
“He’s really the whole package. Successful, confident, happy with himself…if he weren’t my boss, I’d see if there was any potential there. The only concern I’d have is that he doesn’t seem focused on the long-term. From what I’ve heard in industry gossip, he’s on a date with a different woman every week and isn’t even thinking about settling down.”
“A dilemma indeed. You know, maybe we should ask Kerry what she thinks. I know she bats for the other team, but that doesn’t mean she won’t have good relationship insight. Especially when it comes to men in the office and how they treat us.”
“Sure. Let’s see if she’s free for lunch.”
Kerry was the marketing director at RR Apparel, hired away from a career in television where she enjoyed her reporting and production work, but was tired of long hours and wanted to spend more time with her wife Sandy, who had gotten a job as a nurse in a doctor’s office after many years of putting in long hours herself as an ICU floor nurse. They were both looking for more family-friendly jobs to have more time with their son Henry, but Sandy had found a job first. Kerry’s big break came not long after, though, when she met Janet, the company vice president, at a networking event.
“So, Elizabeth, how’s everything?” Kerry asked. “I know we’re starting to plan for the fifth anniversary. I did get your email about what I’ll need help with, and I’m really sorry I didn’t respond to you, but my strategy meeting ran long and then I had a conference call.”
“It’s OK. I figured you had gotten carried away. But listen, you’re confident in yourself and very career-oriented, and I’m not going to go to Janet with this problem because she doesn’t want to hear even an ounce of workplace drama. I’m just curious…what would you do if you felt like you had a crush on someone you worked with? Especially if that someone happened to be higher on the food chain than you.”
“Well, I’d try to be rational. This is a workplace, and we’re all adults working closely together, sometimes for long hours. In this type of environment, it’s easy to see how you can develop feelings for a coworker. However, you also have to be careful. You don’t want everyone to resent you or look down on you because of who you’re dating.”
“That makes sense,” Elizabeth agreed. “I don’t want to give off the appearance that I get special favors or anything either. And what about getting a new job? Is that a solution if you start to develop a crush?”
“If I can cut in, I think that depends on the person,” Shirley said. “I wouldn’t run off immediately. Sometimes crushes fade. Like what if you discovered your coworker snores really loud and you’d never sleep next to them at night? Or they never change the toilet paper when the roll runs out? Then they’re not so appealing and boom, no discomfort on the job.” Everyone laughed at the thought, and Elizabeth briefly pictured Robert as having some annoying habit so she could try to turn off her feelings.
“You see, though,” Elizabeth told Kerry and Shirley. “It’s Robert I’m attracted to. I know, I know; it’s absurd! He’s my boss and you can tell he’s finely walking the line between complimenting me and saying something sexist. However, he’s very charming when he wants to be, and I otherwise like working here. He really respects me too.”
“Interesting,” Kerry said. “I do have to say I wonder if he had more feelings toward you than just those of mutual respect. He usually gets you a little something after his business trips, right? Even if it’s a gift card to a restaurant?”
“Yes, and personally, I’d rather be appreciated than relegated to menial tasks or dumbed down like I was at my last job. After I got hired I told him how my old boss didn’t value me, and he said I wouldn’t have to worry about that here, that I could wear as many hats as I could handle. I never thought it was because he only admired my looks and not my abilities. Now I feel like I should question that. But he’s such an interesting mix of funny and charming and intelligent, even when I think ‘oh God I wish he wouldn’t say some of these things or bring me so many gifts.’”
“You could always try telling him you don’t want as many gifts or that he should stop the compliments and see how he reacts. If he agrees to stop, that means he respects you, but if he doesn’t listen and keeps piling it on, I’d consider discreetly looking for another gig. There’s so many PA jobs in Chicago.”
“You’re right. Gosh, I just don’t understand how I could be annoyed with him and love him at the same time.”
“I could,” Shirley piped up. “That sounds a lot like my marriage, actually. My husband has a lot of quirks that drive me crazy sometimes, but we still love each other. No matter who you date, we all have bad habits and weaknesses. It’s just a matter of what—or who—you’re willing to live with.
“Please don’t leave yet! We have this huge event coming up, and besides, I think you’re everyone’s favorite coworker. You’re like the glue of the office. If worse comes to worst, Janet’s still looking for an assistant; you could ask Robert to transfer and work with her.”
“Somehow that’s even worse. Her standards are so high she’s rejected the last five people she’s interviewed. I heard John’s friend Abby is coming in next week; she was working as an accountant but is looking for something more challenging. John said he tried to explain he doesn’t think that assisting a company VP would be what she’s looking for, but I think she’s looking for a break from endless number crunching and feels bored.”
“I guess I could always be in a worse spot.” Elizabeth sighed. “You know, girls, I think for now, I’ll just see what happens between me and Robert. I’ll keep it as a crush and not try and pursue anything, and if I stay calm and professional, hopefully he won’t notice, right? Oh, and does anyone know a good way to keep yourself from blushing?”
“It’s a natural reaction,” Shirley said. “Not much you can do about that. Just pretend the thermostat isn’t working right and tell him you need to call maintenance to fix it.”
“You know, I really do have a great job. My boss appreciates me, and I have coworkers who will come up with ways to help me hide embarrassing moments and inappropriate crushes. And I admit, I had some of that champagne on New Year’s Eve and took myself out to dinner a few times with those gift cards. Not to mention holiday bonuses that he gives all of us anyway…
“The thing is, now I have to choose. My parents hoped for me to both be successful and find love. I can’t wait to hear their reaction when they find out I’ve been crushing on my boss. Probably wasn’t what they had in mind. And for what it’s worth, I appreciate all of your help.”
When Elizabeth got back to her office, she noticed Robert was already waiting for her. “Nice work while I was gone,” he said. “I already got a call from the Tribune and managed to reschedule. How do you get them on the phone so quickly?”
“I actually just sent the reporter an email. Sometimes it’s easier to get a hold of them that way. I gave him your cell phone number if he wants to reach out to you directly.”
“That’s why I hired you! You know how to work your magic!”
She just hoped that he wasn’t referring to something other than how she got her job done.